Treacherous Waters

Treacherous Waters

Article posted in Retirement Plans on 11 February 2009| 2 comments
audience: Trusts and Estates, National Publication | last updated: 18 May 2011


It just got more dangerous to use income in respect of a decedent for charitable bequests. In this article from the January 2009 issue of Trusts & Estates magazine, UMKC law professor Christopher Hoyt examines how a recent IRS Chief Counsel Memorandum and new proposed regulation will require new strategies to enable donors to successfully pay a charitable bequest with IRD.

By Christopher R. Hoyt

A recent Internal Revenue Service Chief Counsel Memorandum concluded that a trust could not claim a charitable income tax deduction after it had received taxable IRA distributions (that is, income in respect of a decedent or IRD)1 and then distributed the amounts to charities. The ability of an estate or trust to claim a charitable income tax deduction may be further complicated by a new proposed Treasury regulation holding that whenever a governing instrument specifies a source of income (such as IRD) to be used for a charitable income tax deduction, the instructions must have an economic effect independent of income tax consequences in order to be respected.2

In other words, there are new challenges to successfully paying a charitable bequest with IRD—and new strategies are needed to meet them.

What Can Go Wrong

A dramatic illustration of how a charitable bequest of IRD can go wrong can be found in the IRS Chief Counsel Memorandum ILM 200848020, released on Dec. 1, 2008.3

That legal memorandum addressed a situation in which a decedent had left his IRA to a trust benefiting his six children and several charities. The trust received distributions from the IRA for the charitable shares and the trustee immediately paid these amounts to the charities, leaving the six children as the only remaining beneficiaries of the trust. The IRS Chief Counsel’s office concluded that the trust had taxable income from the IRA distributions but was not entitled to claim an offsetting charitable income tax deduction, because the trust document contained no instructions to distribute income to a charity.4

A distribution of IRD to a charity is only deductible if it meets the legal requirement for an estate or trust to claim a charitable income tax deduction. Normally, an estate or trust is not entitled to claim a charitable income tax deduction for the payment of a charitable bequest.5

Yet there have been many instances in which estates and trusts were able to claim a charitable income tax deduction to offset taxable income from IRD.6 To claim a charitable income tax deduction, the charitable payments must be traced7 to income and must generally be made pursuant to the terms of a trust’s governing instrument requiring income be paid to a charity.8 Such instructions apparently were missing from the trust's governing instrument addressed in ILM 200848020. As a result, the IRD was taxed to the trust (or to the children if they received distributions of the trust’s distributable net income (DNI).9)

This Chief Counsel memo prompts the question: Under what circumstances can an estate or trust claim a charitable income tax deduction to offset the taxable income from IRD? Clearly, there is justification for such an income tax deduction under tax policy.10 But what are the mechanics? And what is the impact of the proposed regulation on this arrangement? Because there is no DNI deduction for a distribution to a charity,11 a charitable income tax deduction is essential to get an income tax benefit.

Many wills and trust instruments indeed contain instructions that IRD must be used to satisfy a charitable bequest in the event that the estate or trust has IRD income. A typical provision states: “I instruct that all of my charitable gifts, bequests and devises shall be made, to the extent possible, from ‘income in respect of a decedent’ (as that term is defined under the U.S. income tax laws) included in gross income and shall qualify for a charitable income tax deduction under Section 642(c) of the Internal Revenue Code of 1986 and any corresponding future tax laws.”

If such instructions had appeared in the governing instrument analyzed in ILM 200848020, would the trust have been entitled to an offsetting deduction? Probably.
But, surprisingly, despite the increasing frequency and size of IRD in the estates of the nation’s citizens (particularly retirement plan assets), there is no legal authority on point when instructions in a governing instrument to make a charitable disposition of IRD assured a charitable income tax deduction. There is no court case, regulation or ruling. Legal guidance would be very helpful, as this situation will become increasingly common. By comparison, there is considerable legal authority, that without such instructions there would be a problem claiming a charitable income tax deduction,12 unless the entire estate—or the remainder or residue of an estate—was payable to a charity.13

How is this scenario affected by the proposed regulation that requires an independent economic effect? Ostensibly, the proposed reg merely addresses the division of an estate’s or trust’s taxable and tax-exempt income amongst income beneficiaries, some of which include charities. It does not address whether a charitable income tax deduction will be allowed, denied or partially allowed/denied when a governing instrument contains instructions that all charitable bequests must be satisfied with IRD whenever that is possible.

Some of the provisions can be interpreted in a way that could cause concern. The proposed rule says, “[A] provision in the governing instrument. . . that specifically provides the source out of which amounts are to be paid. . . for such a [charitable] purpose controls for Federal tax purposes to the extent such provision has economic effect independent of income tax consequences.”14 This statement suggests that instructions to use IRD for charitable dispositions might not be respected—unless those dispositions had an independent economic effect. For example, there is no independent economic effect if a will provides for a $100,000 charitable bequest and specifies that it should be “paid from IRD, if any exists.” The charity will receive $100,000 whether there is any IRD or not. Cautious estate planners may consider inserting instructions for charitable uses of IRD that will meet the proposed reg’s criteria of having an economic effect.15

On the other hand, what are the sanctions for failure to have an independent economic effect? The proposed regulation states that the estate’s or trust’s income will be allocated between charitable and non-charitable beneficiaries using the same proportionate ratio of all classes of income of the estate or trust.16 Such a result wouldn’t impose a hardship as long as the estate or trust still could claim a charitable income tax deduction. It wouldn’t matter that the deduction was comprised of a mix of interest, dividends and IRD.

The legal uncertainty about whether an estate or trust can claim a charitable income tax deduction for a distribution of IRD has made alternative ways of structuring charitable bequests of IRD even more attractive. Rather than have IRD payable to an estate or trust that will make a charitable bequest, a better strategy is to bypass the estate or trust entirely and transfer the IRD directly to a charity or to a tax-exempt charitable remainder trust (CRT).

Two Methods

IRD’s classification as taxable income makes it an especially appealing source for funding a charitable bequest. By using taxable IRD payments to satisfy a bequest to a tax-exempt charity, an estate planner can distribute greater amounts of tax-free assets to family members, such as stock or real estate that receive a step up in basis.

There are generally two ways to structure a charitable bequest of IRD. The first is to have the IRD paid directly to a charity so that the charity (rather than an estate, trust or a beneficiary) recognizes all of the IRD income. Because an estate or trust never recognizes any IRD income, there is no need for it to claim an offsetting charitable income tax deduction.  

The second way is to have an estate or trust receive the taxable IRD, then claim an offsetting charitable income tax deduction for the distribution of the IRD to a charity. As the IRS Chief Counsel memorandum illustrates, this strategy should be undertaken only if the estate planner is confident that such an offsetting deduction is assured. With the legal uncertainty concerning the circumstances under which an estate or trust can claim such an offsetting charitable income tax deduction, the first alternative looks increasingly attractive for planning a charitable bequest of IRD.

How can IRD be transferred directly to a charity? The answer depends on the nature and source of the IRD. Is the IRD generated by the type of asset that normally goes through probate, such as savings bonds,17 an employee stock option18 or an installment sale note? Then, the solution can be an in-kind distribution of those assets to a charity so that it, rather than the estate, recognizes the income when payments are received.

The largest amounts of IRD are held in retirement accounts, which are trusts or custodial accounts that usually have their own beneficiary designations. The distributions pass outside of probate, unless the estate was designated as the beneficiary. Consequently, the most common way to transfer the IRD in a retirement plan directly to a charity is for the plan participant or IRA owner to name a charity as a beneficiary of some or all of a retirement account on the beneficiary designation form provided by the plan administrator. In that case, the retirement account makes a payment directly to the charity and informs the charity that the payment is taxable income.

The tax-exempt charity, of course, does not pay income tax upon the receipt of the distribution. This is the case even for a private foundation that must normally pay a 1 percent or 2 percent excise tax on its investment income.19 Under this scenario, the estate or trust never reports the income,20 and consequently, never needs an offsetting charitable income tax deduction.

This strategy also works with other forms of IRD where a person has the ability to designate a beneficiary, such as a bequest of an interest in a nonqualified deferred compensation plan21 or of a taxable death benefit under an annuity contract.22

Thus, instead of having an IRA payable to a trust or an estate that will make a charitable bequest, a safer and simpler strategy is to name the charitable beneficiary directly on the retirement plan form. If the individual in the Chief Counsel memorandum had taken this tact, the income tax problem would have been avoided. The charities would have received their amounts directly from the IRA and the trust would have received only the income intended for the six children. There would be no need for the trust to claim a charitable income tax deduction. As long as the charities received their distributions before Sept. 30 of the year after the decedent’s death, the six children would be eligible to receive the IRA distributions over their life expectancies (stretch IRAs).23

An even safer alternative is to have a separate “charitable IRA” with one IRA administrator (in which all beneficiaries of the IRA are charities and/or tax-exempt charitable remainder trusts) and one or more “family IRAs” with other IRA administrators. Then, there is no time pressure to make the charitable distributions before Sept. 30, because the existence of the charitable IRA has no impact on the mandatory distributions from any of the family IRAs. An individual can keep the asset levels of the charitable IRA and the family IRAs at the desired amounts by withdrawing more or less from each IRA, since an IRA owner’s mandatory lifetime IRA distributions can be taken from any single IRA rather than from every IRA.24
It is even possible to divert payments after death to a charity from an IRA that is payable to an estate. This usually works when the charity will receive the residue of the estate and the personal representative has the power to make non-pro-rata distributions.25 The Service concluded, however, that using retirement assets to satisfy a fixed dollar charitable bequest triggered taxable income to a trust, in which case a charitable income tax deduction is necessary to avoid a tax liability.26
It is especially important for an estate or trust to avoid recognizing income when there is a bequest of IRD to a CRT27 or to acquire a testamentary charitable gift annuity for a beneficiary.28 Any possible charitable income tax deduction would, at best, only partially offset the taxable income from the IRD.29


The legal challenges and complexity for an estate or a trust to obtain a charitable income tax deduction for a charitable bequest of IRD is running smack into the locomotive of an increasing number of estates that have increasing amounts of IRD. Retirement plan assets appeared on 61 percent of all federal estate tax returns filed in 2007 and comprised nearly 7 percent of all reported assets (they were 11.4 percent of the assets reported by estates under $3.5 million).30 The corresponding percentages in 1997 were only 46 percent and 6.2 percent.31 Taxpayers and estate planners need greater certainty and simplicity when leaving retirement assets to an estate or trust with an expectation that those assets will be used to satisfy a charitable bequest.
The Service could improve the efficient administration of tax laws by issuing a revenue ruling or other guidance that taxpayers could rely on for structuring such charitable bequests through their estates or trusts. In the meantime, savvy estate planners will advise their affluent clients to structure their estate plans to have IRD transferred directly to a charity or to a charitable remainder trust in order to avoid having an estate or trust recognize any income. It is Joe Middleclass who, without competent advice, will likely be caught in an income tax trap of having a retirement plan paid to an estate that will make a charitable bequest, thereby triggering an avoidable income tax liability, as evidenced by ILM 200848020.


1. Revenue Ruling 92-47, 1992-1 C.B. 198.

2. Proposed Treasury Regulations Section 1.642(c)-3(b)(2), REG-101258-08, 2008-28 I.R.B. 111.

3. Internal Revenue Service Chief Counsel ILM 200848020 (July 28, 2008), released on Dec. 1, 2008. Such Chief Counsel memoranda have received a variety of designations in citations as either ILM (Internal Legal Memorandum), CCA (Chief Counsel Advice), CA (Counsel Advice) and CCM (Chief Counsel Memorandum). ILM appears most frequently and is therefore used in this article.

4. The Chief Counsel’s office reached a similar conclusion in ILM 200644020 (Dec. 15, 2005). A trust’s use of an IRA to satisfy a fixed dollar charitable bequest was deemed to trigger taxable income to the trust but the trust could not claim an offsetting charitable income tax deduction since there were no instructions in the governing instrument to leave income to charity.

5. See Rev. Rul. 2003-123, 2003-2 C.B. 1200 for the general proposition that a trust cannot claim a charitable income tax deduction for a donation of trust principal as opposed to trust income. The concept is that a charitable bequest is a charitable disposition of property that the decedent owned on the date of death. By comparison, an estate’s income is usually earned after the decedent’s death. Thus, a charitable bequest is usually deducted on an estate’s federal estate tax return rather than the estate’s federal income tax return.

6. See the Private Letter Rulings cited infra note 13.

7. Although other deductions used to be subject to a tracing rule, the laws were changed in 1954 so that the charitable deduction is the principal deduction whose source must still be traced to income. The Tax Court explained the rules and the reason for them in Van Buren v. Commissioner, 89 T.C. 1101 (1987) at 1108-1109.

8. Internal Revenue Code Section 642(c)(1); Treas. Regs. Section 1.642(c)(1)(a)(1). See also Rev. Rul. 83-75, 1983-1 C.B. 114, in which a charitable lead trust’s distribution of appreciated securities to a charity triggered income but the trust was entitled to claim a fully offsetting charitable income tax deduction. See also PLR 9044047 (Aug. 4, 1990).

9. IRC Sections 651, 652, 661 and 662.

10. There is indeed a tax policy justification for allowing an estate or trust to claim a charitable income tax deduction when it uses taxable income in respect of a decedent (IRD) to satisfy a charitable bequest. IRD is different than other income. Whereas an estate’s or trust’s traditional income is earned after death and is only reported on an estate’s income tax return, IRD is income that was earned before death and is potentially reported on both the estate’s income tax return and as an asset on a decedent’s federal estate return. Because IRD is potentially subject to double taxation on both the estate’s federal estate tax return and on its income tax return, a properly structured charitable disposition of the IRD should conceptually qualify for an offsetting charitable deduction on both the estate tax return and the income tax return. It is a different situation than the tax deduction for an estate’s administrative expenses, which can be deducted only on either the income tax return or the estate tax return, but not both. IRC Section 642(g). The potential double taxation of IRD justifies a potential double charitable deduction.

11. IRC Sections 651(a) and 663(a); Rev. Rul. 2003-123, 2003-2 C.B. 1200.

12. See Rev. Rul. 2003-123, 2003-2 C.B. 1200, citing Crestar Bank (Estate Of James A. Linen) v. Internal Revenue Service, 47 F. Supp.2d 670 (E.D. Va. 1999); Van Buren v. Comm’r, 89 T.C. 1101 (1987); and Riggs National Bank v. United States, 352 F. 2d 812 (Ct. Cl. 1965).

13. It is possible for an estate to claim a charitable income tax deduction even in the absence of instructions to distribute income to a charity if the entire estate, or the remainder of an estate, will be paid to a charity. Treas. Regs. Section 1.642(c)-2(d) provides that an estate and certain trusts can claim an income tax charitable set-aside deduction if under the governing instrument the income will be devoted to a charitable purpose and the possibility for any non-charitable use is so remote to be negligible. When an entire estate will be paid to a charity, the income also will be devoted to a charitable purpose. This result also applies when a charity will receive the residue of an estate. After all non-charitable beneficiaries have been paid in full, the only remaining beneficiary of an estate is the charitable remainderman. The Service has permitted estates to claim charitable income tax deductions under these circumstances to offset taxable IRD income. PLRs 200826028 (March 27, 2008), 200526010 (March 22, 2005), 200336030 (June 3, 2003), and 200221011 (Feb. 12, 2002) (IRAs and savings bonds); see also PLR 200537019 (May 25, 2005) (annuity contracts). See also infra note 25 for how distributions from retirement plan accounts that are designated to be paid to an estate or a trust can instead be paid directly to charities so that the estate or trust has no taxable IRD income and, consequently, no charitable income tax deduction is necessary.

14. Prop. Treas. Regs. Section 1.642(c)-3(b)(2).

15. For example: “Pay to charity XYZ all of the taxable retirement plan distributions that my estate receives.” Or: “Pay the first $300,000 of the taxable retirement plan distributions that my estate receives to charity ABC, and the rest of these distributions to my daughter, Natalie.” These examples are variations of illustrations presented by Natalie B. Choate in her well-written article, “Choate on 1.642 and 1.642 Proposed Regs”, LISI Employee Benefits and Retirement Planning Newsletter #462 (Aug. 14, 2008). These clauses have a substantial economic effect, because the charity will receive amounts only if the estate does indeed receive taxable retirement plan distributions. Furthermore, these clauses could “disinherit” other beneficiaries from receiving any or all retirement distributions payable to an estate. Hence, the clauses have an economic effect.

16. “In the absence of such specific provisions in the governing instrument or in local law, the amount to which section 642(c) applies is deemed to consist of the same proportion of each class of the items of income of the estate or trust as the total of each class bears to the total of all classes.” Prop. Treas. Regs. Section 1.642(c)-3(b)(2).

17. Charitable bequests of savings bonds were analyzed in Rev. Rul. 80-118, 1980-1 C.B. 254 and PLR 9845026 (Aug. 11, 1998). See also Treas. Regs. Section 1.691(a)-2(b), Ex. (3).

18. PLRs 200002011 (Sept. 30, 1999) and 200012076 (Dec. 29, 1999) (employee stock options bequeathed to a charity by a will).

19. PLRs 200425027 (Feb. 27, 2004) and 9826040 (March 30, 1998). By comparison, if the IRD consists of interest from savings bonds or an annuity contract, the IRC Section 4940 tax does apply. Rev. Rul. 80-118, 1980-1 C.B. 254 (savings bonds) and PLR 200425027 (Feb. 27, 2004) (annuity contract).

20. Neither the donor’s estate nor heirs will recognize taxable income if retirement plan/IRA proceeds are paid directly to a charity or to a charitable remainder trust. PLRs 200826028 (March 27, 2008), 200652028 (Sept. 13, 2006), 200633009 (May 16, 2006), 200618023 (Jan. 18, 2006), 9723038 (March 11, 1997) (public charity); PLRs 9838028 and 9818009 (private foundation); PLRs 9901023 (Oct. 8, 1998) and 9634019 (May 24, 1996) (charitable remainder trust).

21. PLRs 200002011 (Sept. 30, 1999) and 200012076 (Dec. 29, 1999).

22. PLRs 200425027 (Feb. 27, 2004), 200452004 (Aug. 10, 2004) and 200618023 (Jan 18, 2006).

23. Treas. Regs. Section 1.401(a)(9)-4, Q&A 4. If a trust is a beneficiary of an IRA, then if the trust pays all charitable bequests before Sept. 30 following the year of the IRA owner’s death, the trust may be able to receive “stretched-out” distributions from the IRA payable over the life expectancies of the trust’s designated beneficiaries. See PLR 200740018 (July 12, 2007), in which an IRA was payable to a trust to benefit cousins for life but there was also a pecuniary bequest to a charity. The charity received the entire amount before Sept. 30 following the year of the IRA owner’s death. The Service concluded that the charity was no longer considered a beneficiary of the trust and that the IRA could make distributions to the trust based on the life expectancy of oldest cousin. The Service did not rule on whether the trust could claim a charitable income tax deduction for the charitable payments. This stretch IRA result is what the parties were trying to achieve in ILM 200848020 (July 28, 2008), only to discover that the Service would not allow a charitable income tax deduction.

24. IRS Notice 88-38, 1988-1 C.B. 524.

25. The Service permitted an assignment of IRAs, 401(k) accounts, 403(b) accounts and annuity contracts to charities so that neither the estate nor other beneficiaries had to recognize any taxable income when the retirement accounts made their distributions to the charities. Most rulings applied when the residue of the estate was payable to a charity. PLRs 200826028 (March 27, 2008), 200652028 (Sept. 13, 2006), 200633009 (May 16, 2006), 200618023 (Jan. 18, 2006), 200617020 (Dec. 8, 2005), 200511174 (Feb. 8, 2005), 200526010 (March 22, 2005), and 200452004 (Aug. 10, 2004). Compare PLR 200234019 (May 13, 2002) (IRAs and 403(b) accounts where a portion of the estate went to charity).

26. ILM 200644020 (Dec. 15, 2005), described in supra note 4.   

27. Neither the donor’s estate nor heirs recognized taxable income when retirement plan proceeds were paid after death directly to a charitable remainder trust. PLRs 9901023 (Oct. 8, 1998) and 9634019 (May 24, 1996). For an article on the benefits and hazards of bequeathing retirement assets to a charitable remainder trust, see Christopher R. Hoyt, “When A Charitable Trust Beats A Stretch IRA,” Trusts & Estates, May 2002.

28. In PLR 200230018 (April 22, 2002) an individual named a charity as the beneficiary of an IRA and left instructions with the charity to use the IRA proceeds to issue a charitable gift annuity. The estate recognized no taxable income on the transfer.

29. Only a partial charitable income tax deduction is allowed, because a gift to a charitable remainder trust or to acquire a charitable gift annuity has a non-charitable component (the income stream to the beneficiary). An illustration of the tax nightmare is in PLR 20056024 (April 6, 2005), in which the income tax deduction to acquire charitable gift annuities only partially offset the income tax generated by an IRA withdrawal.

30. IRS statistics on federal estate returns filed in 2007 can be found at

31. Computed from the table at .

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Not all IRD gifts are in Treacherous Waters?

This is an excellent article. If I understand the Article correctly, it appears to apply only to circumstances in which an estate or trust receives IRD, such as an IRA account, and then makes distributions to both taxable and tax exempt charitable beneficiaries . It doesn't appear to apply to estates or trusts which have only charitable beneficiaries. It's not surprising that the IRS would object to situations allowing allocation of taxable income to charity and nontaxable income or assets to taxable individuals, but it would be surprising to me that the IRS would deny a charitable deduction for distributions when all of the beneficiaries are charities. It is possible that some readers of the Article are interpreting it more broadly than you intended, attributing the uncertainty and complexity of situations involving distribution of IRD accounts to an Estate or Trust with subsequent distributions to named beneficiaries even when all the beneficiaries are named charities. If all the beneficiaries of the Estate or Trust are charities, the Article doesn't apply at all, does it? Can this be clarified? Thanks again for this very thought provoking article.

Treacherous Waters, IRD Gifts

Professor Chris Hoyt has again helped the estate planning community and donors with a difficult subject that has enormous impact for the future of charitable giving. As he notes, the difficulty is especially present for donors who, though fully motivated to make an IRD gift, might not have the fully informed and up-to-date advisers working to incorporate all of the most recent IRS rulings. As advisers from the charitable community, we must be sure to keep up with these developments and advise our donors to seek competent counsel when making sizable IRD distributions.

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